34228, Florida, United States Vacation Rental Homes By Owner - Page 17

$321.59

Coastal Comfort - Beach Castle #23 by RVA

Longboat Key, Florida, United States

Relax in this privately owned, coastal-themed ground-floor condo on Longboat Key, perfect for couples or small families. This 1-bedroom, 1-bath vacation rental sleeps up to 4 and offers beautiful bayfront views from the screened lanai, living room, and bedroom.brbrThe condo features a fully equipped kitchen with granite countertops, ice maker, cookware, dishes, Keurig and drip coffee makers, and modern lighting and furnishings. Enjoy a Serta SleepTrue king mattress in the bedroom and a memory-foam sleeper sofa in the living area. Entertainment includes Smart TVs with Roku and cable, complimentary WiFi, games, and books—providing all the comforts of home.brbrBeach Castle Resort is uniquely located on one of the narrowest points of Longboat Key, stretching from the bay to the Gulf of Mexico. Guests enjoy direct private beach access, a bayside fishing dock, and stunning sunrise and sunset views. Spend your days shelling, swimming, fishing, or relaxing on white-sand Gulf beaches. Amenities include a heated community pool, hot tub, grills, complimentary laundry facilities, beach chairs, umbrellas, linens, towels, cooler, and assigned parking.brbrThe beautifully landscaped grounds feature classic Florida charm with Bahama shutters and a peaceful, secluded atmosphere—ideal for creating unforgettable vacation memories. The property is within walking distance to Centre Shops, offering restaurants and ice cream.brbrAs a bonus the owner of Beach Castle 23 has purchased a Complimentary Membership to Cedars East Tennis Resort for all guests. This membership allows access to Har-Tru tennis courts, pickleball, fitness center, Jr. Olympic heated pool, bicycles, and fishing pier.brbrKey Features:br• Walk to Beach: 3–4 minutesbr• Bayfront View and Shared Dockbr• Bedding: 1 King + Sleeper Sofabr• Parking: 1 Assigned Spacebr• Pets: Not Permittedbrbr*Beach Castle is a self-service resort; no daily housekeeping is provided. A starter amenity kit is included upon arrival*brbrBeach Castle Resort on Longboat Key is a destination you’ll want to return to year after year.

1

Bed

1

Bath

4

Sleeps

$264.92

/ Nightly

Condo

Beautiful remodeled 2 Bedroom/2 Bath Longboat Key Condo Overlooking Sarasota Bay

Longboat Key, Florida, United States

Bed

Bath

Sleeps

$300.1

/ Nightly

Private Vacation Home

Pet Friendly LBK Home-Space Galore w Pool, Fireplace & Walk to Beach by RVA

Longboat Key, Florida, United States

RVA presents this spacious vacation home. The Tarawitt Home, is located on a secluded road at the northern tip of Longboat Key. This vacation home has all the amenities needed for a relaxing vacation. With three bedrooms, three baths, a sleeper sofa, and a separate family and game room, the Tarawitt Home can house up to eight persons comfortably. This two-story home sits directly on a canal that leads to Sarasota Bay, and is within walking distance from local shops and dining. Amenities include a private pool, large screened porch, garage parking, a grill, private washer/dryer units. New Home Resource furnishings and a grand fireplace create an atmosphere that is comfortable and casual. With a deeded beach access, the Tarawitt Home is a short walk to the beach -- you are never far from all the necessities of a Florida vacation. Tarawitt Home also welcomes pets, so bring the whole family!brbrbrbrLimited Membership Privileges: Guests of the Tarawitt Home will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Three-bedrooms, three-bathsbrbrbrbrAmenities: Private Patio, Deeded Beach Access, Grill, Wireless Internet, Full-size Kitchen, Pets Allowed, Private Pool, Washer/Dryer, Parking, Entrance to Large Deck from Each Bedroom, Fireplace, Membership Access at Cedars Tennis ResortbrbrbrbrLocation: 741 Tarawitt Drive, Longboat KeybrbrbrbrBedding: 3 Queens, Sleeper SofabrbrbrbrView: Water ViewbrbrbrbrMinimum Night Requirements: Restrictions ApplybrbrbrbrPet Policy: An additional pet fee will be added to applicable bookings. To reserve a pet-friendly booking contact our local team or select the additional pet fee at checkout. Pets not given prior approval will not be accepted.brbrbrbrOther: Additional electric and/or pool heat charges may apply; please call our local offices for details.

Bed

Bath

Sleeps

$244.95

/ Nightly

Condo

Silver Sands Serenity – Unit 234 by RVA

Longboat Key, Florida, United States

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrLimited Membership Privileges: Guests of Silver Sands Gulf Beach Resort #234 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #234 Features: 1-bedroom, 1-bathroom unit in the Blue Garden BuildingbrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Bed

Bath

Sleeps

$327.7

/ Nightly

Condo

Beachplace 8-603 by FGC

Longboat Key, Florida, United States

Experience Coastal Elegance at Beachplace PenthousebrWelcome to Your Dream Beachfront Retreat! brbrDiscover the perfect blend of coastal living and luxury in this stunning Gulf-front penthouse at Beachplace on Longboat Key. As you step inside, you'll be greeted by breathtaking views of the Gulf of Mexico from nearly every room, complemented by a balcony that stretches twice as long as those on other floors.brbrLocated on the sought-after southern end of Longboat Key, Beachplace offers one of the closest buildings to the water, promising an idyllic waterfront lifestyle. This beautifully renovated unit features a large double balcony, ideal for entertaining or simply enjoying the mesmerizing sunset views.brbrDesigned with both comfort and style in mind, the layout boasts raised ceilings throughout, enhancing the spacious feel. Every detail has been thoughtfully curated, from the impact windows and sliders to the gourmet chef's kitchen, which is equipped with top-of-the-line Thermador appliances, custom Euro Tec high-gloss cabinetry, quartz countertops, and a glass tile backsplash.brbrThe large primary suite with King Bed serves as a peaceful retreat, with sliders leading to the balcony. The luxurious primary bath offers a spa-like experience with dual sinks, floating cabinetry with floor lighting, a custom floating ceiling with mood lighting, and heated towel bars. Custom built-in closets provide ample storage, while remote-controlled Hunter Douglas window treatments add a touch of elegance.brSecond bedroom offers one queen bed. Pictures will update soon.brbrAdditional features include a separate laundry/utility room with a full-size LG washer and dryer, and a tankless water heater. Enjoy the convenience of a parking outdoor very near the building, along with resort-style amenities such as a heated Jr. Olympic pool with daily water aerobics, a spa, a canopied baby pool, a clubhouse with weekly yoga classes, two workout rooms, steam rooms, a library, multiple grilling areas, an EV charging station, two pickleball courts, two tennis courts, and an extensive social calendar.brbrHOA only allows rental to be a maximum of 4 people sleeping in condobrStarting September of 2025, the owner will be installing a King bed in Primary bedroom and Queen bed in 2nd Bedroom. brbrIndulge in the ultimate beachfront living experience at Beachplace Penthouse, where every day is a vacation.brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.

Bed

Bath

Sleeps

$316.81

/ Nightly

Condo

Luxury Bayfront Condo | Stunning Views, Pools & Beach Across Street

Longboat Key, Florida, United States

Welcome to Bay Dream Believer, your elegant bayfront retreat on beautiful Longboat Key, Florida. This stunning 2-bedroom, 2-bathroom condo offers panoramic views of Sarasota Bay through massive floor-to-ceiling windows and an enclosed patio that lets you enjoy the scenery year-round. With public beach access just across the street, you’ll experience the best of both worlds — tranquil bayfront living and easy access to the Gulf sands.brbrStep inside to discover a tastefully upgraded interior featuring modern finishes, coastal-inspired décor, and an open layout filled with natural light. The fully equipped kitchen has everything you need to prepare meals at home, while the spacious living and dining areas are perfect for relaxing or entertaining. Both bedrooms are designed for comfort, with the primary suite showcasing incredible bay views and a peaceful ambiance.brbrThe community offers resort-style amenities including two heated swimming pools, convenient elevator access, a fitness center, community kayaks, tennis and pickleball courts, and scenic walking paths along the bay. Reserved parking adds convenience, and pets are welcome upon approval so you can bring your four-legged family member along.brbrWhether you’re here for a short getaway or an extended stay, Bay Dream Believer delivers the perfect mix of comfort, luxury, and coastal charm. Enjoy easy access to St. Armands Circle, Lido Key, and Anna Maria Island, where you’ll find endless shopping, dining, and entertainment options — all just minutes away.brbrBook your stay at Bay Dream Believer and experience why Longboat Key is one of Florida’s most peaceful and picturesque coastal destinations.brbr15 DAY MINIMUM BOOKING PRIOR TO CHECK IN! Association application requires social security numbers.

Bed

Bath

Sleeps

$411.74

/ Nightly

Private Vacation Home

Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

Longboat Key, Florida, United States

What's better than your own private paradise Come and enjoy this beautiful, recently remodeled, canal front 2 bedroom 2 bathroom private home with heated pool located within walking distance to the longboat key beaches. Close proximity to restaurants and a neighborhood atmosphere This beautifully updated elevated 2BR/2 BATH block home features a private setting with 100ft of canal frontage. Private dock, with spectacular view. Across the canal is an undeveloped nature preserve owned by the Town of Longboat Key (no homes).br Fully screened back patio with tons of comfy seating provides ample space for indoor/outdoor living. brThe outdoor area features two lounge chairs, sofa seating with fire pit and additional dining table by the water so you can easily watch for manatee or dolphins.br But, that's not all, there is also a dock so you can bring your boat or rent one from a local marina, do a little fishing or launch kayaks (ask Michaela about the rent)The dock is also equipped with a 10,000 lb. boat lift which is available for use for a small fee to have the lift bunks adjusted to your boat. brMaster Bedroom features a king size bed, 55 smart HD TV and en-suite bathroom.brGuest room features 2 twin size beds , 43 smart HD TV. Fully equipped kitchen. Plenty of pool towels, beach towels and more.....brBEACH ACCESS across Gulf of Mexico Drive on Gulfside drive across from Christ church. We provide a beach wagon, beach chairs &umbrellas.brTo heat the pool during the winter time, we charge $150/week.

Bed

Bath

Sleeps

$345.56

/ Nightly

Condo

Relax, Recharge & Repeat – Silver Sands #241 by RVA

Longboat Key, Florida, United States

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #241 Features: 1-bedroom, 1-bathroom unit in the Green Building with a direct pool view and a distant Gulf view from your private patio.brbrbrbrView: Pool/Gulf ViewbrbrbrbrBedding: 1 King + Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Bed

Bath

Sleeps

$484.25

/ Nightly

Condo

Beachfront Bliss: Beach Castle #1 by RVA

Longboat Key, Florida, United States

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature. brbrbrbrThe grounds here are impeccable – from the well-manicured vegetation to the vast palm trees that dot this serene Longboat Key location. The buildings at Beach Castle are the color of sunshine and are accented by Bahama shutters and railings that resemble palm trees. Each unit is individually owned, which means no unit is alike and provides a unique vacation experience to our guests. However, all units provide a full kitchen, living room and private lanais – never compromising the comforts of home.brbrbrbrThis secluded hideaway exudes a classic charm that, as vacationers, we yearn for. A place to get away from it all, relish in the Florida sunshine and reconnect with family and friends; all this while enjoying white-sand beaches, privacy and most importantly, vacation memories that last a lifetime. brbrbrbrLimited Membership Privileges: Guests of Beach Castle Resort #1 will have the option of temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles, fishing pier and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Beach Castle Resort is a quiet, 21-unit condominium resort midway on the exclusive island of Longboat Key with a variety of views including Gulf front, Bay front, pool and garden views.brbrbrbrUnit #1 Features: Two-bedroom, two-bathroom first-floor unit located on the Gulf side. Decorated in pastels, Florida charm with updated amenities including wireless Internet, granite countertops, updated appliances, and LCD, flat-screen TV’s. Netflix available.brbrbrbrView: Gulf Front ViewsbrbrbrbrBedding: 1 King, 2 Queens, Sleeper SofabrbrbrbrParking: All guests have use of 1 assigned parking spot during their stay. Additional spots are available at a nearby community on a first-come, first-served basis. We kindly ask guests to plan accordingly.brbrbrbrPets: Pets are not permitted on Beach Castle property.brbrbrbrResort Features: Full-size Kitchen, Spacious Floorplans, Heated Community Pool, Community Hot Tub, Grills, On-site Office, Private Lanais, Complimentary Laundry Facilities, Shared Boat Docks (available on a first-come, first-served basis, a 26' boat limit, and guest is responsible to find off-site parking for boat trailer), Cable TV, Wireless Internet, Complimentary Guest Parking, Private Beach Access, Complimentary Lounge Chairs and UmbrellasbrbrbrbrPlease Note: Beach Castle is a self service resort; we do not provide daily housekeeping services. For your convenience, an amenity “Starter Kit” is provided to assist you upon your arrival. Any essentials required after the initial provided, such as toilet paper, dish soap, etc. is the responsibility of the guest.

Bed

Bath

Sleeps

$287.68

/ Nightly

Condo

Gulfside Getaway – Silver Sands Resort #235 by RVA

Longboat Key, Florida, United States

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrLimited Membership Privileges: Guests of Silver Sands Gulf Beach Resort #235 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #235 Features: 2-bedroom, 2-bathroom unit in the Blue Gardens BuildingbrbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, 2 Twins, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Bed

Bath

Sleeps

$412.95

/ Nightly

Condo

2BR Gulf View Condo Cabana Beach Club #7 by RVA

Longboat Key, Florida, United States

RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambiance and relaxed atmosphere of this vacation hideaway, coupled with the natural foliage and perfect location have created a must-see community on Longboat Key. The attention to detail, from the cleanliness of your unit to the manicured grounds, will be evident the moment you arrive. The glorious sunrises, the romantic sunsets, the lush tropical flowers abloom everywhere - you will believe you have found a personal paradise in the Cabana Beach Club. Many of our guests return year-after-year to relax and enjoy the area’s many attractions. Resort amenities include a heated swimming pool, community laundry facilities and complimentary chaise lounges.brbrbrbrAccommodations: Cabana Beach Club is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key with several units also located on the bay side. Choose from our various unit styles including one-, two-bedroom and efficiency units. Enjoy all the amenities of home in these fully furnished condominiums including TVs, full-sized kitchen or kitchenette, dining room, and modern, beach-styled decorations.brbrbrbrResort Features: Heated Swimming Pool, Private Beach Access, Internet Access (select units), Complimentary Chaise Lounge Chairs, Fully Equipped Kitchens or Kitchenettes, Barbeque Area, Private Patio or Lanai, Community Laundry Facilities, Outdoor Shower, Various ViewsbrbrbrbrUnit #7 Features: This two-bedroom plus den, two-bath unit is the largest at Cabana Beach Club and will easily accommodate 6 guests. Recent renovations include a beautiful new full-sized kitchen with granite countertops, all new stainless steel appliances, a full-sized washer and dryer in the unit, updated bathroom, and wireless Internet access. The outdoor lanai overlooking the pool is the perfect spot for morning coffee. Best of all, the beach is only steps away! Don’t wait, your perfect vacation is just a click away.brbrbrbrView: Gulf Front ViewbrbrbrbrBedding: 2 Kings, 1 day Bed/trundle

Bed

Bath

Sleeps

$332.24

/ Nightly

Condo

Outrigger #8 Condo by RVA Peaceful Gulf

Longboat Key, Florida, United States

RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger Resort. The Outrigger grounds offer coin-operated laundry facilities, BBQ areas, and direct beach access. Relax by the heated community pool, take a stroll along the romantic beaches, or enjoy a short drive to the world famous St. Armand's Circle. This one-bedroom, one-bath Gulf front unit offers beautiful decor and views. Relax on your private screened lanai and escape to paradise.brbrbrbrAccommodations: One-bedroom, one-bathroombrbrbrbrAmenities: Private Lanai, Grill, Full-size Kitchen, Wireless Internet, Community Pool, Washer/Dryer, On the Beach, Private Beach AccessbrbrbrbrLocation: 5155 Gulf of Mexico Drive, Longboat KeybrbrbrbrBedding: 1 KingbrbrbrbrView: Gulf Front ViewbrbrbrbrMinimum Night Restrictions: 7 Nights; Contact our local team for shorter stay options

Bed

Bath

Sleeps

$288.15

/ Nightly

Condo

Charming 2-bedroom condo overlooking Sarasota Bay on Longboat Key

Longboat Key, Florida, United States

Escape to this brilliant condo in picturesque Longboat Key. This cozy retreat features 2 bedrooms with a king bed and full bathroom, and twin beds with full bathroom, perfect for a small group of guests. Enjoy the serene atmosphere and modern amenities like a fitness room , BBQ area, heated swimming pools. One over looking our lanai and Sarasota Bay. Or if prefer , you can walk across the street to our deeded private gulf beach. No trucks allowed. Our place will help you feel at home while enjoying your stay

Bed

Bath

Sleeps

$297.76

/ Nightly

Private Vacation Home

Tropical Canal Home–Pool, Sun & Water Access: Paradise Cottage in LBK by RVA

Longboat Key, Florida, United States

Prime Location! Discover this newly decorated seasonal rental on Longboat Key's picturesque canal. Nestled in South Longboat Key, it offers seamless access to St. Armands Circle, Lido Key, and downtown Sarasota. This inviting single-family home boasts two bedrooms, two and a half bathrooms, a spacious living/dining area, a bonus Florida room with cozy seating and a TV. The well-equipped kitchen features ample counter space, cabinets, and a breakfast nook. Unwind in the generously sized master bedroom with a king-sized bed and ensuite bathroom, while the guest bedroom offers two twin beds. brbrbrbrStep onto the expansive lanai to relish multiple seating areas providing the perfect setting for al fresco dining or leisurely lounging. Enjoy panoramic views of the canal and the azure waters of the private pool. Garage parking for one car. Pet-free environment. Don't miss out on this seasonal gem in Longboat Key, Florida!brbrbrbrAccommodations: Two-bedroom, two-and-half-bathbrbrbrbrAmenities: Private Patio, Grill, Private Heated Pool, Fire Pit, Full-size Kitchen, Washer/Dryer, Wireless Internet AccessbrbrbrbrLocation: 524 Yawl Ln, Longboat KeybrbrbrbrBedding: 1 Kings, 1 Queen, 1 FutonbrbrbrbrView: Canal Viewbrbrbrbr30 Day Minimum Night RequirementbrbrbrbrOther: Additional electric and/or pool heat charges may apply; please call our local offices for details.

2

Bed

2

Bath

6

Sleeps

$351.37

/ Nightly

Condo

Renovated 2BR/2BA condo - Buttonwood Cove 103C by FVC

Longboat Key, Florida, United States

Welcome to your Longboat Key getaway at Buttonwood Cove 103C, a beautifully renovated 2-bedroom, 2-bath condo where comfort, style, and island charm come together. Perfectly positioned in one of Longboat Key’s most desirable communities, this inviting retreat offers stunning views of Sarasota Bay along with private beach access just across Gulf of Mexico Drive.brbrInside, you’ll find a fresh, recently renovated interior with tasteful finishes, comfortable furnishings, and an open layout designed for easy coastal living. The spacious living area flows seamlessly to the screened lanai, where you can enjoy morning coffee, evening cocktails, or simply relax while taking in the peaceful bay views and warm Florida breezes.brbrBoth bedrooms are thoughtfully furnished with king beds, making this condo an ideal retreat for couples, friends, or seasonal guests seeking both comfort and privacy. The primary suite features an en-suite bath, while the guest bedroom and second full bath offer a welcoming setup for additional guests.brbrButtonwood Cove is known for its beautifully maintained grounds and outstanding amenities, including a waterfront heated pool, tennis courts, fishing pier, kayak launch, clubhouse, and deeded private beach access directly across the street on the Gulf side. Spend your days enjoying the best of both worlds, sunrise views over the bay and sunset walks on the beach.brbrLocated on the peaceful north end of Longboat Key, you’ll be just minutes from local dining, shopping, and the boutiques and restaurants of St. Armands Circle.brbrWhether you’re planning a winter retreat or an extended island escape, this Buttonwood Cove condo offers the perfect combination of updated style, resort-style amenities, bayfront serenity, and private beach access. brbrProfessionally managed by Florida Vacation Connection.

2

Bed

2

Bath

4

Sleeps

$174.13

/ Nightly

Condo

Gulf of Mexico Direct Gulf View Condo

Longboat Key, Florida, United States

Welcome to your perfect Gulf Coast getaway! This stunning 2-bedroom, 2-bathroom condo offers breathtaking, direct views of the Gulf of Mexico, right from your own private balcony. Located in the highly sought-after Seaplace community, you’ll enjoy a peaceful, gated environment with resort-style amenities.brbrFeatures & Amenities:brbrSpectacular Gulf Views br2 Spacious Bedrooms with comfortable, modern furnishingsbr2 Full Bathrooms with updated fixtures and plenty of spacebrFully Equipped Kitchen perfect for preparing meals or entertainingbrPrivate Balcony to enjoy the sunset, ocean breeze, and panoramic viewsbr2 Heated Pools & 2 Hot Tubs for relaxing after a day at the beachbrDirect Beach Access just steps away from the condobrLocated Next to the Newly Built St. Regis Hotel, offering extra dining and entertainment options nearbybrbrWhether you're relaxing on the beach, lounging by the pool, or enjoying the local area, this condo is the ultimate spot to unwind. With top-tier amenities and a prime location, it’s the perfect retreat for families, couples, or friends.brbrBook your stay today and experience the best of coastal living!

Bed

Bath

Sleeps

$241.88

/ Nightly

Apartment

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

Longboat Key, Florida, United States

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large resort with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck, so guests can read email, surf the Internet and soak up the Florida sun all at the same time!brbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including studio rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrUnit #247A Features: Studio in the Orange BuildingbrbrBedding: 1 Queen brbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Daily Maid Service, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, DVD/VHS Players, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Bed

Bath

Sleeps

$305.6

/ Nightly

Private Vacation Home

Pet-Friendly 2BR Condo–Cedars East #810 by RVA

Longboat Key, Florida, United States

Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations.brbrbrDiscover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gulf Coast. Imagine waking up in a spacious, beautifully appointed townhome—perfect for families seeking fun-filled adventures or couples looking for a romantic retreat.brbrbrHere, every day is an invitation to indulge. Step outside and be greeted by world-class tennis courts, ideal for both casual play and competitive matches. Dive into the sparkling junior Olympic-sized swimming pool or enjoy a rejuvenating workout at the state-of-the-art fitness center. Cast a line from the fishing pier, explore the island on complimentary bicycles, or simply unwind as you watch tropical sunsets paint the sky in unforgettable hues.brbrbrAccommodations: Cedars Tennis Resort is a village-like town home community that features spacious living and dining areas and full-size kitchens. Enjoy all the amenities of home in these fully furnished condominiums including full-sized kitchen with breakfast bar, separate dining area and private lanai (available in select units).brbrbrClub and Recreation Facilities: Tennis and Pickleball Courts - 10 Har-Tru (soft-clay) tennis courts with professional instruction, daily clinics, round robins, and seasonal tournaments. Newly designed pickleball courts. brbrbrPro-Shop - Onsite Pro-Shop for equipment, apparel, and help with court reservations. brbrbrSwimming Pool and Tiki Bar - A heated Junior Olympic-sized pool with complimentary chaise lounges. Seasonal Tiki Bar adjacent to the pool. brbrbrFitness Center - Modern, 24/7 accessible fitness center with secure access. brbrbrBicycles for Guests - Adult-sized bikes available for daily use—ideal for exploring Gulf of Mexico Drive. brbrbrDining and Social Spaces - Hugo II Restaurant - A European Fusion restaurant offering German, Czech, and Italian dishes plus specialty Prosecco cocktails; private dining memberships required (no extra cost for Club members). Open Seasonally.brbrbrClubhouse and Social Areas - Clubroom, bar area, and recreational spaces enhance the communal experience. brbrbrFishing Pier and Mangrove Boardwalks - Charming wooden boardwalks wind through mangroves, leading to a serene fishing pier—perfect for picnics or watching boats and marine life. brbrbrBeach Access Information - The beautiful Gulf of Mexico shoreline stretches north and south along Longboat Key, and guests are welcome to enjoy it by using any designated Public Beach Access point. These access points are clearly marked with signs indicating Public use. Please note: Private beach access points along Gulf of Mexico Drive are reserved for property owners and their guests. Unless an access point is clearly labeled as Public it is not available for use. We encourage you to explore and enjoy the public areas of the beach and thank you for respecting local property boundaries.brbrbrResidential and Guest Accommodations - Townhomes - Tri-level, spacious units featuring full-size kitchens, screened lanais or private balconies, and comfortable living/dining areas. The community is divided into three sections—The Gardens (500s), Club Level (600s), and Preserves (800s)—all connected via picturesque boardwalks.brbrbrUnit #810 Accommodations: 2-bedroom, 2.5 bathroom townhome with views of the bay and preserve from your private patio. Pet Policy: Only accepts non shedding pets weighing less than 35 lbs. To reserve a pet-friendly booking contact our local team or select the additional pet fee at checkout. Pets not given prior approval will not be accepted.brbrbrUnit Amenities: 1-Car Garage, Wireless Internet, Full-size Kitchen, Private Lanai, 24/7 Fitness Facility, Community Pool, Beach Access (A Short Distance Away).brbrbrbrLocation: 810 Evergreen Place, Longboat KeybrbrbrbrView: Bay ViewbrbrbrbrBedding: 1 King, Full-Size Bunkbeds + 1 Additional TwinbrbrbrbrMinimum Night Requirements: Minimum stays apply

Bed

Bath

Sleeps

$262.69

/ Nightly

Condo

Relax at Gulf – Silver Sands Resort #232, Longboat

Longboat Key, Florida, United States

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck, so guests can read email, surf the Internet and soak up the Florida sun all at the same time!brbrbrbrLimited Membership Privileges: Guests of Silver Sands #232 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #232 Features: 1-bedroom, 1-bathroom unit adjacent to the office brbrbrbrView: Garden ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

1

Bed

1

Bath

4

Sleeps

$357.29

/ Nightly

Condo

Harbour Hideout: Condo on Longboat Key by RVA

Longboat Key, Florida, United States

Enjoy elevated views that span the harbourside greens from the comfort of the 3BD/2BA villa residence positioned behind the private gates of Bay Isles on Longboat Key. Spacious upon entry, you are met with a foyer that opens to a combined living and dining area which further leads into a family room and kitchen space. These, along with the master bedroom, are positioned to front the golf course and offer terrace access; a place for a perfect afternoon of warm relaxation within an expanse of pleasing greenery. The location of this unit is ideal for receiving the peaceful and quiet vacation you deserve; while still in close reach of attractions and activities of cultural downtown Sarasota. brbrbrWake up in the morning to the sounds of birds chirping and plan a full day of visiting St. Armands Circle, enjoying a pleasant bike ride around the island, taking a dip in the sparkling community pool, feeling the warmth of the Gulf of Mexico, or venturing to downtown Sarasota. The Longboat Key lifestyle is one of a kind and it is waiting for you.brbrbrbrOther details of this residence include beach access thru the Bay Isles Beach Club where you can have a picnic and grill, partake in a volleyball game, and shower off before heading home. brbrbrbrAccommodations: Three-bedroom, two-bathbrbrbrbrAmenities: Private Balcony, Beach Access, Full-size Kitchen, Community Pool, Community Hot Tub, Tennis Courts at Bayfront Park, Wireless Internet Access, Washer/DryerbrbrbrbrLocation: 2115 Harbourside Dr., Longboat KeybrbrbrbrBedding: 2 King, 1 QueenbrbrbrbrView: Golf Course ViewbrbrbrbrMinimum Night Requirements: 1 MonthbrbrbrbrAssociation Requirements: $100 Fee + Application + 30-Day Approval Time

3

Bed

2

Bath

6

Sleeps

34228, Florida, United States Vacation Rental Homes By Owner - Page 17

$321.59

$264.92

$300.1

$244.95

$327.7

$316.81

$411.74

$345.56

$484.25

$287.68

$412.95

$332.24

$288.15

$297.76

$351.37

$174.13

$241.88

$305.6

$262.69

$357.29

Rent a place that suits your needs

Most popular vacation rentals in Longboat Key

$884.08

$746.18

$747.69

$755.36

$767.89

$861.14

$1148.84

$2112.85

$1196.70

$739.37

Most Popular Cities in Florida